Water → 3-Methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acid

HRID 2164335Notes

Reaction equation

HRID 2164335 reaction equation
C[O:2][C:3]([C:5]1[O:16][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[C:6]=1[O:23][CH3:24])=[O:4].[OH-].[Na+].O>CO>[CH3:24][O:23][C:6]1[C:7]2[N:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]=2[O:16][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13220385HCID 13220385, compound

Product 1

HCID 132203943-Methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 13.5 g (0.042 mole) of 3-methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic acid methyl ester in 75 ml of methanol was treated with 70.6 ml of 1.0N aqueous sodium hydroxide. The mixture was stirred at reflux for 17 hours, then added to 1.4 l of water. The insoluble material was filtered, added to 1.0 l of water, and acidified with acetic acid while cooling in an ice bath. The crude acid product was recovered by filtration. The original filtrate from the reaction mixture and 1.4 l of water was also cooled in ice and acidified with acetic acid. The crude product obtained was filtered and combined with the earlier crop. The combined crude products were stirred in 400 ml of water, filtered, and recrystallized from methanol. There are obtained 5.8 g (45% yield) of analytically pure acid, mp 154°-155° C.

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationThe insoluble material was filtered
  3. additionadded to 1.0 l of water
  4. temperaturewhile cooling in an ice bath
  5. filtrationThe crude acid product was recovered by filtration
  6. temperatureThe original filtrate from the reaction mixture and 1.4 l of water was also cooled in ice

Sources & evidence

ORD record
ord-ff75efe93967467383a97ed42f11bd65
Source dataset
uspto-grants-1985_03
Patent number
US04503236

Reaction notes

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